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Antidiabetic effect of Ardisia elliptica extract and its mechanisms of action in STZ-NA-induced diabetic rat model via 1H-NMR-based metabolomics

Wong PL, Zolkeflee NKZ, Ramli NS, Tan CP, Azlan A, Tham CL, et al.

J Ethnopharmacol, 2024 Jan 10;318(Pt B):117015.
PMID: 37572932 DOI: 10.1016/j.jep.2023.117015

ETHNOPHARMACOLOGICAL RELEVANCE: Ardisia elliptica Thunb. (AE) (Primulaceae) is a medicinal plant found in the Malay Peninsula and has been traditionally used to treat diabetes. However, limited studies to date in providing scientific evidence to support the antidiabetic efficacy of this plant by in-vitro and in-vivo models.
AIM OF THE STUDY: To investigate the anti-hyperglycemic potential of AE through in-vitro enzymatic activities and streptozotocin-nicotinamide (STZ-NA) induced diabetic rat models using proton-nuclear magnetic resonance (1H-NMR)-based metabolomics approach.
MATERIALS AND METHODS: Anti-α-amylase and anti-α-glucosidase activities of the hydroethanolic extracts of AE were evaluated. The absolute quantification of bioactive constituents, using ultra-high performance liquid chromatography (UHPLC) was performed for the most active extract. Three different dosage levels of the AE extract were orally administered for 4 weeks consecutively in STZ-NA induced diabetic rats. Physical assessments, biochemical analysis, and an untargeted 1H-NMR-based metabolomics analysis of the urine and serum were carried out on the animal model.
RESULTS: Type 2 diabetes mellitus (T2DM) rat model was successfully developed based on the clear separation observed between the STZ-NA induced diabetic and normal non-diabetic groups. Discriminating biomarkers included glucose, citrate, succinate, allantoin, hippurate, 2-oxoglutarate, and 3-hydroxybutyrate, as determined through an orthogonal partial least squares-discriminant analysis (OPLS-DA) model. A treatment dosage of 250 mg/kg body weight (BW) of standardized 70% ethanolic AE extract mitigated increase in serum glucose, creatinine, and urea levels, providing treatment levels comparable to that obtained using metformin, with flavonoids primarily contribute to the anti-hyperglycemic activities. Urinary metabolomics disclosed that the following disturbed metabolism pathways: the citrate cycle (TCA cycle), butanoate metabolism, glycolysis and gluconeogenesis, pyruvate metabolism, and synthesis and degradation of ketone bodies, were ameliorated after treatment with the standardized AE extract.
CONCLUSIONS: This study demonstrated the first attempt at revealing the therapeutic effect of oral treatment with 250 mg/kg BW of standardized AE extract on chemically induced T2DM rats. The present study provides scientific evidence supporting the ethnomedicinal use of Ardisia elliptica and further advances the understanding of the fundamental molecular mechanisms affected by this herbal antidote.
Clinicians' diagnostic practice of dengue infections

Ng CF, Lum LC, Ismail NA, Tan LH, Tan CP

J Clin Virol, 2007 Nov;40(3):202-6.
PMID: 17928264 DOI: 10.1016/j.jcv.2007.08.017

BACKGROUND: Difficulties in the classification of dengue infection have been documented. Such difficulties could be due to the low awareness of the World Health Organization diagnostic guidelines among clinicians.
OBJECTIVE: To study the diagnostic practices of clinicians in classifying patients as dengue fever (DF) or dengue haemorrhagic fever (DHF)/dengue shock syndrome (DSS) at the time of discharge during an outbreak.
METHODS: A prospective descriptive study of clinical features and disease classification in adult and pediatric dengue patients in the University of Malaya Medical Centre.
RESULTS: Five hundred and twenty adult and 191 pediatric patients were enrolled. Thrombocytopenia and evidence of plasma leakage were present in 8% of adult and 19% of pediatric patients. Of these, 93% and 49%, respectively, were given the discharge diagnoses of DF instead of DHF/DSS. Hemoconcentration, serous effusion and thrombocytopenia were not recognized in clinicians' discharge diagnosis of DHF/DSS for adult patients. The receiver operating characteristic (ROC) curve suggested a lack of consistency in the use of WHO guidelines in establishing DHF/DSS in adult patients, while implying otherwise for pediatric patients.
CONCLUSION: DHF/DSS is an under-recognized condition by clinicians managing these patients. This can affect the case fatality rate of DHF/DSS and the economic burden of the disease. The lack of awareness in disease manifestations especially plasma leakage, can lead to delayed recognition of DHF/DSS.
Study site: Outpatient department and inpatients, adult medical and pediatric wards, University Malaya Medical Center (UMMC), Kuala Lumpur, Malaysia
Analysis of 1,2(2,3)- and 1,3-positional isomers of diacylglycerols from vegetable oils by reversed-phase high-performance liquid chromatography

Lo SK, Baharin BS, Tan CP, Lai OM

J Chromatogr Sci, 2004 Mar;42(3):145-54.
PMID: 15023251

Separation of 1,2(2,3)- and 1,3-positional isomers of diacylglycerols (DAG) from vegetable oils by reversed-phase high-performance liquid chromatography (RP-HPLC) is investigated. The method is based on isocratic elution using 100% acetonitrile and UV detection at 205 nm. The following elution order of DAG molecular species is identified: 1,3-dilinolein < 1,2-dilinolein < 1,3-dimyristin < 1-oleoyl-3-linoleoyl-glycerol < 1,2-dimyristoyl-rac-glycerol < 1(2)-oleoyl-2(3)-linoleoyl-glycerol < 1-linolenoyl-3-stearoyl-glycerol < 1(2)-linolenoyl-2(3)-stearoyl-glycerol < 1,3-diolein < 1-palmitoyl-3-oleoyl-glycerol < 1,2-dioleoyl-sn-glycerol < 1(2)-palmitoyl-2(3)-oleoyl-glycerol < 1-linoleoyl-3-stearoyl-glycerol < 1,3-dipalmitin < 1(2)-linoleoyl-2(3)-stearoyl-glycerol < 1-oleoyl-3-stearoyl-glycerol < 1,2-dipalmitoyl-rac-glycerol < 1-palmitoyl-3-stearoyl-sn-glycerol < 1,3-distearin < 1,2-distearoyl-rac-glycerol. Linearity is observed over three orders of magnitude. Limits of detection and quantitation range 0.2-0.7 microg/mL for 1,3-dilinolein to 0.6-1.9 microg/mL for 1,2-dioleoyl-sn-glycerol, respectively. Precision and accuracy of the method are also demonstrated. The method is developed to separate mixtures of DAG molecular species produced from edible oils.
Characterization of bovine serum albumin partitioning behaviors in polymer-salt aqueous two-phase systems

Chow YH, Yap YJ, Tan CP, Anuar MS, Tejo BA, Show PL, et al.

J Biosci Bioeng, 2015 Jul;120(1):85-90.
PMID: 25553974 DOI: 10.1016/j.jbiosc.2014.11.021

In this paper, a linear relationship is proposed relating the natural logarithm of partition coefficient, ln K for protein partitioning in poly (ethylene glycol) (PEG)-phosphate aqueous two-phase system (ATPS) to the square of tie-line length (TLL(2)). This relationship provides good fits (r(2) > 0.98) to the partition of bovine serum albumin (BSA) in PEG (1450 g/mol, 2000 g/mol, 3350 g/mol, and 4000 g/mol)-phosphate ATPS with TLL of 25.0-50.0% (w/w) at pH 7.0. Results also showed that the plot of ln K against pH for BSA partitioning in the ATPS containing 33.0% (w/w) PEG1450 and 8.0% (w/w) phosphate with varied working pH between 6.0 and 9.0 exhibited a linear relationship which is in good agreement (r(2) = 0.94) with the proposed relationship, ln K = α' pH + β'. These results suggested that both the relationships proposed could be applied to correlate and elucidate the partition behavior of biomolecules in the polymer-salt ATPS. The influence of other system parameters on the partition behavior of BSA was also investigated. An optimum BSA yield of 90.80% in the top phase and K of 2.40 was achieved in an ATPS constituted with 33.0% (w/w) PEG 1450 and 8.0% (w/w) phosphate in the presence of 8.5% (w/w) sodium chloride (NaCl) at pH 9.0 for 0.3% (w/w) BSA load.
Direct recovery of cyclodextringlycosyltransferase from Bacillus cereus using aqueous two-phase flotation

Lin YK, Show PL, Yap YJ, Tan CP, Ng EP, Ariff AB, et al.

J Biosci Bioeng, 2015 Dec;120(6):684-9.
PMID: 26111602 DOI: 10.1016/j.jbiosc.2015.04.013

Purification of cyclodextrin glycosyl transferase (CGTase) from Bacillus cereus using polyethylene glycol (PEG)-potassium phosphates aqueous two-phase flotation (ATPF) system was studied in this paper. The effects of varying PEG molecular weight, tie-line length (TLL) value, volume ratio (VR), pH value, crude concentration and gas nitrogen flotation time were investigated. The optimal condition for purification of CGTase was attained at 18.0% (w/w) PEG 8000, 7.0% (w/w) potassium phosphates, VR of 3.0, 20% (w/w) crude load at pH 7, and 80 min nitrogen flotation time at a flow rate of 5 L/min. With this optimal condition, purification factor (PFT) of 21.8 and a yield (YT) of 97.1% were attained. CGTase was successfully purified in a single downstream processing step using the ATPF.
Effect of organic-phase solvents on physicochemical properties and cellular uptake of astaxanthin nanodispersions

Anarjan N, Tan CP, Ling TC, Lye KL, Malmiri HJ, Nehdi IA, et al.

J Agric Food Chem, 2011 Aug 24;59(16):8733-41.
PMID: 21726079 DOI: 10.1021/jf201314u

A simplex centroid mixture design was used to study the interactions between two chosen solvents, dichloromethane (DCM) and acetone (ACT), as organic-phase components in the formation and physicochemical characterization and cellular uptake of astaxanthin nanodispersions produced using precipitation and condensation processes. Full cubic or quadratic regression models with acceptable determination coefficients were obtained for all of the studied responses. Multiple-response optimization predicted that the organic phase with 38% (w/w) DCM and 62% (w/w) ACT yielded astaxanthin nanodispersions with the minimum particle size (106 nm), polydispersity index (0.191), and total astaxanthin loss (12.7%, w/w) and the maximum cellular uptake (2981 fmol/cell). Astaxanthin cellular uptake from the produced nanodispersions also showed a good correlation with their particle size distributions and astaxanthin trans/cis isomerization ratios. The absence of significant (p > 0.05) differences between the experimental and predicted values of the response variables confirmed the adequacy of the fitted models.
Optimization of processing parameters for the preparation of phytosterol microemulsions by the solvent displacement method

Leong WF, Che Man YB, Lai OM, Long K, Misran M, Tan CP

J Agric Food Chem, 2009 Sep 23;57(18):8426-33.
PMID: 19694442 DOI: 10.1021/jf901853y

The purpose of this study was to optimize the parameters involved in the production of water-soluble phytosterol microemulsions for use in the food industry. In this study, response surface methodology (RSM) was employed to model and optimize four of the processing parameters, namely, the number of cycles of high-pressure homogenization (1-9 cycles), the pressure used for high-pressure homogenization (100-500 bar), the evaporation temperature (30-70 degrees C), and the concentration ratio of microemulsions (1-5). All responses-particle size (PS), polydispersity index (PDI), and percent ethanol residual (%ER)-were well fit by a reduced cubic model obtained by multiple regression after manual elimination. The coefficient of determination (R(2)) and absolute average deviation (AAD) value for PS, PDI, and %ER were 0.9628 and 0.5398%, 0.9953 and 0.7077%, and 0.9989 and 1.0457%, respectively. The optimized processing parameters were 4.88 (approximately 5) homogenization cycles, homogenization pressure of 400 bar, evaporation temperature of 44.5 degrees C, and concentration ratio of microemulsions of 2.34 cycles (approximately 2 cycles) of high-pressure homogenization. The corresponding responses for the optimized preparation condition were a minimal particle size of 328 nm, minimal polydispersity index of 0.159, and <0.1% of ethanol residual. The chi-square test verified the model, whereby the experimental values of PS, PDI, and %ER agreed with the predicted values at a 0.05 level of significance.
Modeling the relationship between the main emulsion components and stability, viscosity, fluid behavior, zeta-potential, and electrophoretic mobility of orange beverage emulsion using response surface methodology

Mirhosseini H, Tan CP, Hamid NS, Yusof S

J Agric Food Chem, 2007 Sep 19;55(19):7659-66.
PMID: 17708646

The possible relationships between the main emulsion components (namely, Arabic gum, xanthan gum, and orange oil) and the physicochemical properties of orange beverage emulsion were evaluated by using response surface methodology. The physicochemical emulsion property variables considered as response variables were emulsion stability, viscosity, fluid behavior, zeta-potential, and electrophoretic mobility. The independent variables had the most and least significant ( p < 0.05) effect on viscosity and zeta-potential, respectively. The quadratic effect of orange oil and Arabic gum, the interaction effect of Arabic gum and xanthan gum, and the main effect of Arabic gum were the most significant ( p < 0.05) effects on turbidity loss rate, viscosity, viscosity ratio, and mobility, respectively. The main effect of Arabic gum was found to be significant ( p < 0.05) in all response variables except for turbidity loss rate. The nonlinear regression equations were significantly ( p < 0.05) fitted for all response variables with high R (2) values (>0.86), which had no indication of lack of fit. The results indicated that a combined level of 10.78% (w/w) Arabic gum, 0.56% (w/w) xanthan gum, and 15.27% (w/w) orange oil was predicted to provide the overall optimum region in terms of physicochemical properties studied. No significant ( p > 0.05) difference between the experimental and the predicted values confirmed the adequacy of response surface equations.
Diacylglycerol and triacylglycerol as responses in a dual response surface-optimized process for diacylglycerol production by lipase-catalyzed esterification in a pilot packed-bed enzyme reactor

Lo SK, Cheong LZ, Arifin N, Tan CP, Long K, Yusoff MS, et al.

J Agric Food Chem, 2007 Jul 11;55(14):5595-603.
PMID: 17571899

Diacylglycerol (DAG) and triacylglycerol (TAG) as responses on optimization of DAG production using a dual response approach of response surface methodology were investigated. This approach takes the molecular equilibrium of DAG into account and allows for the optimization of reaction conditions to achieve maximum DAG and minimum TAG yields. The esterification reaction was optimized with four factors using a central composite rotatable design. The following optimized conditions yielded 48 wt % DAG and 14 wt % TAG: reaction temperature of 66.29 degrees C, enzyme dosage of 4 wt %, fatty acid/glycerol molar ratio of 2.14, and reaction time of 4.14 h. Similar results were achieved when the process was scaled up to a 10 kg production in a pilot packed-bed enzyme reactor. Lipozyme RM IM did not show any significant activity losses or changes in fatty acid selectivity on DAG synthesis during the 10 pilot productions. However, lipozyme RM IM displayed higher selectivity toward the production of oleic acid-enriched DAG. The purity of DAG oil after purification was 92 wt %.
Optimization of palm oil physical refining process for reduction of 3-monochloropropane-1,2-diol (3-MCPD) ester formation

Zulkurnain M, Lai OM, Tan SC, Abdul Latip R, Tan CP

J Agric Food Chem, 2013 Apr 3;61(13):3341-9.
PMID: 23464796 DOI: 10.1021/jf4009185

The reduction of 3-monochloropropane-1,2-diol (3-MCPD) ester formation in refined palm oil was achieved by incorporation of additional processing steps in the physical refining process to remove chloroester precursors prior to the deodorization step. The modified refining process was optimized for the least 3-MCPD ester formation and acceptable refined palm oil quality using response surface methodology (RSM) with five processing parameters: water dosage, phosphoric acid dosage, degumming temperature, activated clay dosage, and deodorization temperature. The removal of chloroester precursors was largely accomplished by increasing the water dosage, while the reduction of 3-MCPD esters was a compromise in oxidative stability and color of the refined palm oil because some factors such as acid dosage, degumming temperature, and deodorization temperature showed contradictory effects. The optimization resulted in 87.2% reduction of 3-MCPD esters from 2.9 mg/kg in the conventional refining process to 0.4 mg/kg, with color and oil stability index values of 2.4 R and 14.3 h, respectively.
Phospholipid-Protein Structured Membrane for Microencapsulation of DHA Oil and Evaluation of Its In Vitro Digestibility: Inspired by Milk Fat Globule Membrane

Chen Y, Ge H, Zheng Y, Zhang H, Li Y, Su X, et al.

J Agric Food Chem, 2020 Jun 03;68(22):6190-6201.
PMID: 32379465 DOI: 10.1021/acs.jafc.0c01250

The present study aims to design a milk fat globule membrane (MFGM)-inspired structured membrane (phospholipid- and protein-rich) for microencapsulation of docosahexaenoic acid (DHA) oil. DHA-enriched oil emulsions were prepared using different ratios of sunflower phospholipid (SPL), proteins [whey protein concentrate (WPC), soy protein isolate (SPI), and sodium caseinate (SC)], and maltodextrin and spray-dried to obtain DHA microcapsules. The prepared DHA oil emulsions have nanosized particles. SPLs were found to affect the secondary structure of WPC, which resulted in increased exposure of the protein hydrophobic site and emulsion stability. SPL also reduced the surface tension and viscosity of the DHA oil emulsions. In vitro digestion of the spray-dried DHA microcapsules showed that they were able to effectively resist gastric proteolysis and protect their bioactivity en route to the intestine. The DHA microcapsules have a high lipid digestibility in the small intestine with a high DHA hydrolysis efficiency (74.3%), which is higher than that of commercial DHA microcapsules.
Interactions between Food Hazards and Intestinal Barrier: Impact on Foodborne Diseases

Li X, Tan CP, Liu YF, Xu YJ

J Agric Food Chem, 2020 Dec 16;68(50):14728-14738.
PMID: 33289375 DOI: 10.1021/acs.jafc.0c07378

The intestine is an important digestive organ of the human body, and its barrier is the guardian of the body from the external environment. The impairment of the intestinal barrier is believed to be an important determinant in various foodborne diseases. Food hazards can lead to the occurrence of many foodborne diseases represented by inflammation. Therefore, understanding the mechanisms of the impact of the food hazards on intestinal barriers is essential for promoting human health. This review examined the relationship between food hazards and the intestinal barrier in three aspects: apoptosis, imbalance of gut microbiota, and pro-inflammatory cytokines. The mechanism of dysfunctional gut microbiota caused by food hazards was also discussed. This review discusses the interaction among food hazards, intestinal barrier, and foodborne diseases and, thus, offers a new thought to deal with foodborne disease.
Understanding of the Role of Pretreatment Methods on Rapeseed Oil from the Perspective of Phenolic Compounds

Xu YJ, Jiang F, Song J, Yang X, Shu N, Yuan L, et al.

J Agric Food Chem, 2020 Aug 19;68(33):8847-8854.
PMID: 32806128 DOI: 10.1021/acs.jafc.0c03539

The thermal pretreatment of oilseed prior to oil extraction could increase the oil yield and improve the oil quality. Phenolic compounds are important antioxidants in rapeseed oil. In this study, we investigated the impact of thermal pretreatment method on the rapeseed oil based on phenolic compound levels. Liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) analysis showed that the phenolic compound contents in the microwave-pretreated oil were higher than those in the oven- and infrared-treated oils. Sinapic acid (SA) and canolol (CA), which are the top two phenolic compounds in rapeseed oil, exerted well 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity with IC50 values of 8.45 and 8.80 μmol/L. The cell experiment uncovered that SA and CA have significant biological activities related to rapeseed oil quality, including increase of antioxidant enzymes superoxide dismutase (SOD), alleviation of reactive oxygen species (ROS), and cytotoxicity of HepG2 cells after the intake of excessive oleic acid. Further investigation indicated that SA and CA reduced cell apoptosis rate through Bax-Bcl-2-caspase-3 and p53-Bax-Bcl-2-caspase-3, respectively. Taken together, our findings suggest that microwave pretreatment is the best method to improve the content of phenolic compounds in rapeseed oil compared with oven and infrared pretreatments.
Effect of Purification Methods on the Physicochemical and Thermodynamic Properties and Crystallization Kinetics of Medium-Chain, Medium-Long-Chain, and Long-Chain Diacylglycerols

Wang S, Lee WJ, Wang Y, Tan CP, Lai OM, Wang Y

J Agric Food Chem, 2020 Aug 05;68(31):8391-8403.
PMID: 32511921 DOI: 10.1021/acs.jafc.0c01346

Medium-chain diacylglycerol (MCD), medium-long-chain diacylglycerol (MLCD), and long-chain diacylglycerol (LCD) were prepared through enzymatic esterification using different conditions at temperatures of 55-70 °C and reaction times of 1.5-5 h and in the presence of 5-6% Novozym 435. Subsequently, purification was performed using three different techniques, namely, molecular distillation (MD), deodorization (DO), and silica gel column chromatography (SGCC). Variations in terms of the physicochemical and thermodynamic properties, crystallization properties, and kinetics of the diacylglycerols (DAGs) before and after purification were determined. Irrespective of the DAG chain lengths, SGCC was able to produce samples with high DAG purity (96-99 wt %), followed by MD (58-79 wt %) and DO (39-59 wt %). A higher 1,3-DAG/1,2-DAG ratio was recorded for all samples, with the highest ratio recorded for SGCC purified samples. Regardless of the purification techniques used, the solid fat content (SFC) profiles of crude samples with steep curves were altered post-purification, showing a gradual increment in SFC along with increasing temperature. Modification of the Avrami constant and coefficient suggested the modification of the crystal growth mechanism post-purification. Crystallization and melting temperatures of products with a higher DAG purity were shifted to a higher temperature region. Variations were also reflected in terms of the crystal polymorphism, whereby the α and β' crystals transitioned into the more stable β form in purified samples accompanied by modification in the microstructures and crystal sizes. However, there was insignificant change in the morphology of MLCD crystal after purification, except for the decrease in crystal sizes. In conclusion, synthesis of MCD, MLCD, and LCD comprising different DAG purities had distinctive SFC profiles, thermodynamic properties, crystallization kinetics, and crystal morphologies, which can be further incorporated into the preparation of a variety of fat products to obtain end products with desired characteristics.
Encapsulation of Ethylene Gas into Granular Cold-Water-Soluble Starch: Structure and Release Kinetics

Shi L, Fu X, Tan CP, Huang Q, Zhang B

J Agric Food Chem, 2017 Mar 15;65(10):2189-2197.
PMID: 28215072 DOI: 10.1021/acs.jafc.6b05749

Ethylene gas was introduced into granular cold-water-soluble (GCWS) starches using a solid encapsulation method. The morphological and structural properties of the novel inclusion complexes (ICs) were characterized using scanning electron microscopy, X-ray diffractometry, and Raman spectroscopy. The V-type single helix of GCWS starches was formed through controlled gelatinization and ethanol precipitation and was approved to host ethylene gas. The controlled release characteristics of ICs were also investigated at various temperature and relative humidity conditions. Avrami's equation was fitted to understand the release kinetics and showed that the release of ethylene from the ICs was accelerated by increasing temperature or RH and was decelerated by increased degree of amylose polymerization. The IC of Hylon-7 had the highest ethylene concentration (31.8%, w/w) among the five starches, and the IC of normal potato starch showed the best controlled release characteristics. As a renewable and inexpensive material, GCWS starch is a desirable solid encapsulation matrix with potential in agricultural and food applications.
Choline-Chloride-Based Eutectic Solvent for the Efficient Production of Docosahexaenoyl and Eicosapentaenoyl Ethanolamides via an Enzymatic Process

Liang H, Qin X, Tan CP, Li D, Wang Y

J Agric Food Chem, 2018 Nov 21;66(46):12361-12367.
PMID: 30394748 DOI: 10.1021/acs.jafc.8b04804

Docosahexaenoyl and eicosapentaenoyl ethanolamides (DHEA and EPEA) have physiological functions, including immunomodulation, brain development, and anti-inflammation, but their efficient production is still unresolved. In this study, choline-chloride-based natural deep eutectic solvents are used as media to improve the production of DHEA and EPEA. The water content showed a key effect on the reactant conversion. Adding water to choline chloride-glucose (CG, molar ratio of 5:2) led to a significant increase (13.03% for EPEA and 27.95% for DHEA) in the yields after 1 h. The high yields of EPEA (96.84%) and DHEA (90.06%) were obtained under the optimized conditions [fish oil ethyl esters/ethanolamine molar ratio of 1:2, temperature of 60 °C, 1 h, enzyme loading of 2195 units, and CG containing 8.50% water of 43.30% (w/w, relative to total reactants)]. The products could be easily separated using centrifugation. In summary, the research has the potential to produce fatty acyl ethanolamides.
Effects of Environmental Stresses and in Vitro Digestion on the Release of Tocotrienols Encapsulated Within Chitosan-Alginate Microcapsules

Tan PY, Tan TB, Chang HW, Tey BT, Chan ES, Lai OM, et al.

J Agric Food Chem, 2017 Dec 06;65(48):10651-10657.
PMID: 29124932 DOI: 10.1021/acs.jafc.7b03521

Considering the health benefits of tocotrienols, continuous works have been done on the encapsulation and delivery of these compounds. In this study, we encapsulated tocotrienols in chitosan-alginate microcapsules and evaluated their release profile. Generally, these tocotrienols microcapsules (TM) displayed high thermal stability. When subjected to pH adjustments (pH 1-9), we observed that the release of tocotrienols was the highest (33.78 ± 0.18%) under basic conditions. The TM were also unstable against the effect of ionic strength, with a high release (70.73 ± 0.04%) of tocotrienols even at a low sodium chloride concentration (50 mM). As for the individual isomers, δ-tocotrienol was the most sensitive to pH and ionic strength. In contrast, β-/γ-tocotrienols were the most ionic-stable isomers but more responsive toward thermal treatment. Simulated gastrointestinal model showed that the chitosan-alginate-based TM could be used to retain tocotrienols in the gastric and subsequently release them in the intestines for possible absorption.
Natural Organochlorines as Precursors of 3-Monochloropropanediol Esters in Vegetable Oils

Tiong SH, Saparin N, Teh HF, Ng TLM, Md Zain MZB, Neoh BK, et al.

J Agric Food Chem, 2018 Jan 31;66(4):999-1007.
PMID: 29260544 DOI: 10.1021/acs.jafc.7b04995

During high-temperature refining of vegetable oils, 3-monochloropropanediol (3-MCPD) esters, possible carcinogens, are formed from acylglycerol in the presence of a chlorine source. To investigate organochlorine compounds in vegetable oils as possible precursors for 3-MCPD esters, we tested crude palm, soybean, rapeseed, sunflower, corn, coconut, and olive oils for the presence of organochlorine compounds. Having found them in all vegetable oils tested, we focused subsequent study on oil palm products. Analysis of the chlorine isotope mass pattern exhibited in high-resolution mass spectrometry enabled organochlorine compound identification in crude palm oils as constituents of wax esters, fatty acid, diacylglycerols, and sphingolipids, which are produced endogenously in oil palm mesocarp throughout ripening. Analysis of thermal decomposition and changes during refining suggested that these naturally present organochlorine compounds in palm oils and perhaps in other vegetable oils are precursors of 3-MCPD esters. Enrichment and dose-response showed a linear relationship to 3-MCPD ester formation and indicated that the sphingolipid-based organochlorine compounds are the most active precursors of 3-MCPD esters.
Comparative Lipidomic Analysis Reveals the Lactational Changes in the Lipid Profiles of Chinese Human Milk

Wu D, Zhang L, Tan CP, Zheng Z, Liu Y

J Agric Food Chem, 2023 Apr 05;71(13):5403-5416.
PMID: 36951298 DOI: 10.1021/acs.jafc.2c08857

Human milk (HM) lipid plays a crucial role in infant development, whereas its complex lipid profiles and its dynamic changes during prolonged lactation have not been investigated yet. Comparative lipidomic analyses were employed in investigating the lipid profiles of breast milk covering all lactation stages herein. Results revealed significant differences between colostrum and the remaining lactations. A total of 237 species of glycerolipids (GLs) and 231 phospholipids (PLs) were identified. Colostrum had the most abundant lipid species and was enriched with triacylglycerols (TGs) with a high molecular weight. TG(17:1/18:1/24:1), TG(24:1/24:1/26:1), TG(24:0/24:1/26:1), and SM(d20:1/14:1) were characteristic lipids of colostrum. Differential lipid species which were responsible for distinguishing the adjacent lactations were also indicated. Our findings can help deepen the overall understanding of HM lipid profiles and its dynamic changes, which will facilitate the development of infant formulas suitable for Chinese babies in diverse age groups.
Prevention of Hypercholesterolemia with "Liposomes in Microspheres" Composite Carriers: A Promising Approach for Intestinal-Targeted Oral Delivery of Astaxanthin

Liu A, He M, Liu C, Ye Z, Tan CP, Liu Y, et al.

J Agric Food Chem, 2024 Mar 27;72(12):6118-6132.
PMID: 38477232 DOI: 10.1021/acs.jafc.3c08697

Cardiovascular diseases are caused by hypercholesterolemia. Astaxanthin (AST) has been reported to exhibit antioxidant and anti-inflammatory properties. However, its bioavailability is poor because of low solubility and instability. In order to improve the bioavailability of AST, we developed an intestinal-responsive composite carrier termed as "liposomes in micropheres" incorporating N-succinyl-chitosan (NSC)-poly(ethylene glycol) (PEG) liposomes that functionalized by neonatal Fc receptors (FcRn) into hydrogels of sodium alginate (SA) and carboxymethyl chitosan (CMCS). In the AST NSC/HSA-PEG liposomes@SA/CMCS microspheres, the AST's encapsulation efficiency (EE) was 96.26% (w/w) and its loading capacity (LC) was 6.47% (w/w). AST NSC/HSA-PEG liposomes had stability in the gastric conditions and achieved long-term release of AST in intestinal conditions. Then, AST NSC/HSA-PEG liposomes@SA/CMCS bind to intestinal epithelial cell targets by the neonatal Fc receptor. In vitro permeation studies show that there was a 4-fold increase of AST NSC/HSA-PEG liposomes@SA/CMCS in AST permeation across the intestinal epithelium. Subsequent in vivo experiments demonstrated that the composite carrier exhibited a remarkable mucoadhesive capacity, allowing for extended intestinal retention of up to 12 h, and it displayed deep penetration through the mucus layer, efficiently entering the intestinal villi epithelial cells, and enhancing the absorption of AST and its bioavailability in vivo. And oral administration of AST NSC/HSA-PEG liposomes@SA/CMCS could effectively prevent hypercholesterolemia caused by a high-fat, high-cholesterol diet (HFHCD). These advancements highlight the potential of NSC/HSA-PEG liposomes@SA/CMCS composite carriers for targeted and oral uptake of hydrophobic bioactives.

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